toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester → 1-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene

HRID 30603Notes

Reaction equation

HRID 30603 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([F:21])[CH2:9]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:5]=[CH:6][CH:7]=1.[CH2:22]([Mg]Br)[CH:23]=[CH2:24]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C@@H:8]([F:21])[CH2:9][CH2:24][CH:23]=[CH2:22])[CH:3]=1

Participants

4

Reactant 2

HCID 59790335toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl esterHCID 178455850HCID 178455850, compound

Product 1

HCID 686490871-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester (5 mmol) in THF at room temperature is treated dropwise with a 1M solution of allylmagnesium bromide, stirred at room temperature for 5 h, quenched with saturated NH4Cl and extracted with ethyl acetate. The extracts are combined, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to afford 1-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene.

Workup

  1. customquenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. washwashed sequentially with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5904cd7f23f453db929e9aa454f32c8
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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